The proposed work of this project is the synthesis of conformationally eclipsed rigid analogs of ephedrine. The compounds to be prepared are cis and trans 2-methyl-3-phenylazetidin-3ol and cis and trans 2-phenyl-2-hydroxycyclobutylamine. These compounds will be separated into their enantiomeric forms and the use of optical rotatory dispersion and circular dichroism as a method of configuration assignment will be investigated. Once the compounds are obtained pharmacological studies on isolated adrenergically inervated tissues will be carried out. These studies of ephedrine analogs should give a better insight as to the absolute structural requirements of adrenergic agents for interaction with neuroeffector and/or uptake and metabolic sites. This knowledge should lead to a much better understanding of adrenergic drugs and their mechanism of action at the molecular level.